US2023105913A1PendingUtilityA1
Condensed cyclic compound, organic light emitting device including condensed cyclic compound, and electronic apparatus including organic light emitting device
Est. expiryApr 23, 2041(~14.7 yrs left)· nominal 20-yr term from priority
Inventors:Eunkyung LeeYongsik JungSangdong KimJuhyun KimYusuke MaruyamaSangyeon HwangInkoo KimJiwhan KimSungho NamDaun Jeong
H10K 85/658H10K 2101/20C09K 11/06H10K 50/121C07F 5/027H10K 2102/351H10K 85/322H10K 50/11H10K 2101/10H10K 50/12C09K 2211/1018H01L 51/008H01L 51/5016H10K 85/6572H10K 2101/90H10K 85/657
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Claims
Abstract
Provided are a condensed cyclic compound represented by one of Formulae 1 to 4, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the organic light-emitting device:Formulae 1 to 4 may respectively be understood by referring to the descriptions Formulae 1 to 4 provided herein.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A condensed cyclic compound represented by one of Formulae 1 to 4:
wherein, in Formulae 1 to 4,
Y 1 is B, N, P, or P(═O),
A 1 to A 3 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
X 1 is O, S, Se, N(R 10 ), C(R 10 )(R 20 ), Si(R 10 )(R 20 ), Ge(R 10 )(R 20 ), or P(═O)(R 10 ),
X 2 is O, S, Se, N(R 30 ), C(R 30 )(R 40 ), Si(R 30 )(R 40 ), Ge(R 30 )(R 40 ), or P(═O)(R 30 ),
X 3 is a single bond, O, S, Se, N(R 50 ), C(R 50 )(R 60 ), Si(R 50 )(R 60 ), Ge(R 50 )(R 60 ), or P(═O)(R 50 ),
Ar 1 to Ar 7 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
a1 to a5 are each 1, 2, or 3,
R 1 to R 5 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ),
b1 to b3 are each independently an integer from 1 to 10,
a substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, -CD 3 , -CD 2 H, -CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD 3 , -CD 2 H, -CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), or any combination thereof;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD 3 , -CD 2 H, -CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), or any combination thereof;
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), or —P(═O)(Q 38 )(Q 39 ); or
any combination thereof,
wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 3 -C 10 cycloalkyl group; a C 1 -C 10 heterocycloalkyl group; a C 3 -C 10 cycloalkenyl group; a C 1 -C 10 heterocycloalkenyl group; a C 6 -C 60 aryl group unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a C 6 -C 60 aryloxy group; a C 6 -C 60 arylthio group; a C 1 -C 60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
2 . The condensed cyclic compound of claim 1 , wherein A 1 to A 3 in Formulae 1 to 4 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a fluorene group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.
3 . The condensed cyclic compound of claim 1 , wherein Ar 1 to Ar 7 in Formulae 1 to 4 are each independently a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
4 . The condensed cyclic compound of claim 1 , wherein Ar 1 to Ar 7 in Formulae 1 to 4 are each independently: a cyclopentane group, a cyclohexane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, a pentalene group, an indene group, an azulene group, a heptalene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, or any combination thereof.
5 . The condensed cyclic compound of claim 1 , wherein Ar 1 to Ar 5 in Formulae 1 to 3 are each independently a group represented by one of Formulae Ar-1 to Ar-3, and Ar 6 and Ar 7 in Formula 4 are each independently a group represented by Formula Ar-4:
wherein, in Formulae Ar-1 to Ar-4,
X 21 to X 24 are each independently C or N,
Z 1 is deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a carbazolyl group,
d1 is an integer from 0 to 4,
d2 is an integer from 0 to 3, and
*, *′, and *″ each indicate a binding site to an adjacent atom.
6 . The condensed cyclic compound of claim 1 , wherein a moiety represented by
in Formula 4 is represented by one of Formulae 4-1 to 4-4:
wherein, in Formulae 4-1 to 4-4,
Z 1 and Z 2 are each independently: deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a carbazolyl group,
d2 and d3 are each independently an integer from 0 to 3,
R 10 and R 20 are respectively understood by referring to the descriptions of R 21 and R 22 in claim 1 , and
* and *′ each indicate a binding site to an adjacent atom.
7 . The condensed cyclic compound of claim 1 , wherein R 1 to R 5 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 in Formulae 1 to 4 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof; a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —N(Q 31 )(Q 32 ), or any combination thereof; a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, —N(Q 31 )(Q 32 ), or any combination thereof; or —N(Q 1 )(Q 2 ), wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently: a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C 1 -C 10 alkyl group, a phenyl group, or any combination thereof.
8 . The condensed cyclic compound of claim 1 , wherein R 1 to R 5 , R 10 , R 20 , R 30 , R 40 , R 50 , and R 60 in Formulae 1 to 4 are each independently:
hydrogen, deuterium, —F, or a cyano group; a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; or —N(Q 1 )(Q 2 ), wherein Q 1 and Q 2 are each independently: a C 1 -C 10 alkyl group; a C 1 -C 10 alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C 1 -C 10 alkyl group, a phenyl group, or any combination thereof.
9 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by Formula 1A, Formula 2A, Formula 3A, or Formula 4A:
wherein, in Formulae 1A, 2A, 3A, and 4A,
Ar 11 and Ar 12 are each understood by referring to the descriptions of Ar 1 in claim 1 ,
Ar 31 and Ar 32 are each understood by referring to the descriptions of Ar 3 in claim 1 , and
X 1 , X 2 , A 1 to A 3 , Ar 1 to Ar 7 , R 1 to R 5 , and b1 to b3 are respectively understood by referring to the descriptions of X 1 , X 2 , A 1 to A 3 , Ar 1 to Ar 7 , R 1 to R 5 , and b1 to b3 in claim 1 .
10 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by Formula 1A-1, Formula 2A-1, Formula 3A-1, or Formula 4A-1:
wherein, in Formulae 1A-1, 2A-1, 3A-1, and 4A-1,
b11, b22, and b31 are each independently an integer from 1 to 3,
b12 and b21 are each independently an integer from 1 to 4,
b32 is an integer of 1 or 2,
Ar 11 and Ar 12 are each understood by referring to the descriptions of Ar 1 in claim 1 ,
Ar 31 and Ar 32 are each understood by referring to the descriptions of Ar 3 in claim 1 , and
X 1 , X 2 , Ar 1 to Ar 7 , and R 1 to R 5 are respectively understood by referring to the descriptions of X 1 , X 2 , Ar 1 to Ar 7 , and R 1 to R 5 in claim 1 .
11 . The condensed cyclic compound of claim 10 , wherein Ar 11 , Ar 12 , Ar 2 , Ar 31 , Ar 32 , Ar 4 , and Ar 5 in Formulae 1A-1 to 3A-1 are each independently a group represented by one of Formulae Ar-1 to Ar-3, and Ar 6 and Ar 7 in Formula 4A-1 are each independently a group represented by Formula Ar-4:
wherein, in Formulae Ar-1 to Ar-4,
X 21 to X 24 are each independently C or N,
Z 1 is deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a carbazolyl group,
d1 is an integer from 0 to 4,
d2 is an integer from 0 to 3, and
*, *′, and *″ each indicate a binding site to an adjacent atom.
12 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by Formula 1A-2, Formula 2A-2, Formula 3A-2, or Formula 4A-2:
wherein, in Formulae 1A-2, 2A-2, 3A-2, and 4A-2,
b11, b22, and b31 are each independently an integer from 1 to 3,
b12 and b21 are each independently an integer from 1 to 4,
b32 is an integer of 1 or 2,
Z 1 , Z 2 and Z 11 to Z 16 are each independently deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a carbazolyl group,
d1 and d11 to d16 are each independently an integer from 0 to 4,
d2 and d3 are each independently an integer from 0 to 3, and
X 1 , X 2 , and R 1 to R 5 are respectively understood by referring to the descriptions of X 1 , X 2 , and R 1 to R 5 in claim 1 .
13 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by one of Compounds 1 to 40:
14 . An organic light-emitting device comprising: a first electrode,
a second electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer comprises at least one condensed cyclic compound of claim 1 .
15 . The organic light-emitting device of claim 14 , wherein the emission layer comprises the condensed cyclic compound.
16 . The organic light-emitting device of claim 14 , wherein the emission layer comprises a host and a dopant, and the dopant comprises the condensed cyclic compound.
17 . The organic light-emitting device of claim 15 , wherein the emission layer emits delayed fluorescence.
18 . The organic light-emitting device of claim 15 , wherein the emission layer emits blue light.
19 . The organic light-emitting device of claim 14 , wherein the emission layer comprises a host, an emitter, and a sensitizer, the host, the emitter, and the sensitizer are different from one other, and the condensed cyclic compound is comprised in the emitter.
20 . An electronic apparatus comprising the organic light-emitting device of claim 14 .Join the waitlist — get patent alerts
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